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Dimethylformamide → 7-isobutyryl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 51506
Notes
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Reaction equation

HRID 51506 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[O:7]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:28]3[C:27]([NH2:29])=[N:26][CH:25]=[N:24][C:23]=3[NH:22][CH:21]=2)=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C=O>N1C=CC=CC=1>[C:1]([N:22]1[C:23]2[N:24]=[CH:25][N:26]=[C:27]([NH2:29])[C:28]=2[C:20]([C:17]2[CH:16]=[CH:15][C:14]([O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:19][CH:18]=2)=[CH:21]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 62325Isobutyryl chlorideHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 227363967-isobutyryl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

Isobutyryl chloride (1.8 g) was added dropwise to a mixture of 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (4.32 g), dry dimethyl-formamide (200 ml) and dry pyridine (2 ml) with stirring under nitrogen at 20° C. The mixture was stirred at ambient temperature for 1 hour and evaporated under vacuum. The residue was partitioned between water and ethyl acetate. The ethyl acetate was separated, dried and evaporated and the residue obtained was recrystallised from toluene to give 7-isobutyryl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 160.5-161° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 1 hour
  2. customevaporated under vacuum
  3. customThe residue was partitioned between water and ethyl acetate
  4. customThe ethyl acetate was separated
  5. customdried
  6. customevaporated
  7. customthe residue obtained
  8. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-b977410907254daabd8a9c7bcaa27135
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713474B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes